Leadership Fellows Program

Oct 25, 2024 6:00PM—Oct 27, 2024 12:00PM


Santa Barbara Inn

Cost $5,300 members; $7,900 non-members

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Leadership Fellows Program


RETREAT: October 25 - 27, 2024  at Santa Barbara Inn

SESSION 1: December 13, 2024 | 10:00am - 12:00pm | Virtual

SESSION 2: January 10, 2025 | 10:00am - 3:00pm | Hotel Amarano in Burbank, CA


SESSION 3: March 14, 2025 | 10:30am - 3:30pm | Location TBD With a Happy Hour following


Priority Applications are Due by May 15!

The job of an independent school leader can be complicated and rewarding–and on some days, it’s pretty darn tough. Often working directly with many constituent groups, school leaders require a myriad of interpersonal and professional skills in order to lead, to collaborate effectively, and to have impact. With an ever-more complicated world landscape, it’s essential to not only be an effective leader but also make the work joyful and sustainable by better knowing oneself and the needs of the position.

This Fellowship for experienced educators from throughout California supports the unique demands of independent school leaders—the only program of its kind in the state! Facilitated by two Heads of School (one former and one current), the Leadership Fellows Program offers time for personal reflection on one’s leadership journey, practical knowledge and skill development specifically targeted to independent school leadership, as well as supportive professional connections.

The program opens with a two-day retreat in Santa Barbara designed to allow the cohort to connect and reflect as well as engage in sessions designed to hone leadership capacities. Other sessions might include case studies, problem-based discussions, career planning and strategy, and activities that will challenge participants to reflect on their roles and encourage the development of their leadership skills.


  • To provide experienced preK-12 leaders with the knowledge, skills, and resources important for senior level leadership;
  • To provide time and space to “see oneself” clearly and reflect on where each person is–uniquely–in their leadership journey;
  • To address topics such as leadership EQ, communication, team building, systems thinking, strategic planning, and organizational health;
  • To develop and strengthen relationships and networks of support among school leaders.

CATDC is delighted to structure Leadership Fellows in primarily an in-person model with three in person meetings and one on-line meeting We begin with a two night retreat in Santa Barbara, a virtual cohort check in, and two day-long sessions, one in Northern and one in Southern California. In addition, participants will visit a colleague’s school in their area and have a virtual individual mentoring session with one of the facilitators.


Individuals who are or aspire to be senior leaders and/or heads of school. Preferably participants will have five years experience in a leadership capacity in academic roles (academic deans, division directors or deans of curriculum/teaching and learning, DEI) or non-academic ones (admissions, development, communications, or finance).


Leadership fellows is honestly the best kept secret in terms of professional development for headship. I was privileged to be a part of the second cohort of this group and the relationships formed there and the coaching I received are why I am able to confidently serve as a head of school now. I continue to lean on those connections and feel fully supported even now – I can’t speak highly enough of this opportunity and encourage everyone interested in serving as a head to make the commitment!

I had no idea how much I would learn from my cohort group, and how bonded we would become during this process. The role playing was incredibly helpful, and all the guest speakers brought excellent (and differing) perspectives to the conversation.

I loved that the group was coming from different types of schools (sizes, grades, etc.). Building those bonds is what is the most important to me! The program leaders are both invested and extremely knowledgeable.

I appreciated knowing that not everyone in the program wants to be a director, that there are other ways to lead. Also, It was reaffirming to hear that other schools are having the same issues as mine, and seeing perspectives from other departments was extremely helpful and opened my eyes to some other job opportunities.


Enrollment in this program is limited and by application only. Requirements for consideration of admission to this program include: 

  • Application submission: Priority applications are due May 15 with our first round of participants announced June 1.   If there is still space left in the program, a second round of applications will be due on September 15 with our full cohort announced on October 1. Please find our application form here.
  • A $500 program deposit to be submitted via Eventbrite, refunded if you are not accepted.


Phil Gutierrez headshot

Phil Gutierrez is the Head of School at Marin Primary & Middle School in Larkspur, CA. Before MP&MS, he was the Head of School at Mid-Peninsula High School in Menlo Park, CA. Prior to headship, Phil worked at The Branson School in Ross, CA for 22 years, first as an English teacher and then in a variety of administrative roles, including class dean, Director of Admission, and Assistant Head of School for Advancement and External Affairs. Phil currently serves on the boards of CATDC, CAIS, and Live Oak School, and he previously served on the Mark Day School board. He is also on the faculty of the NAIS School Leadership Institute in Washington DC. Phil holds his B.A. in English, with a minor in Spanish, from U.C. Berkeley and his M.A. from Stanford. His wife, Robbie, works at Marin Academy. Their daughter is in college; their son will start college in the fall of 2023. Phil loves to play the guitar, read, and entertain the family's black Labrador retriever.


Crystal Land (she/her) is currently a Senior Associate for Leadership + Design. Crystal has spent her career leading and teaching in independent schools. Following 30 years at the Head-Royce School in Oakland, California, Crystal recently retired as the Head of School where she previously served in a variety of roles from Assistant Head of School and Admissions Director to English teacher. Crystal studies and applies the best practices in authentic and effective leadership and thrives on mentoring others. She has designed and facilitated workshops for school leaders in the Bay Area and nationwide on topics including strategic planning, developing capacity and collaboration in leadership teams, school governance and conflict resolution. Crystal currently serves on the board of directors of CATDC and is involved in supporting first generation college students through the Oakland Promise and the Heads Up program. She holds a M.A. in English from Middlebury College, a M.A. in Education from Stanford University and a B.A. from U.C. Berkeley in English and Political Science. Crystal and her husband, Will Miller, live in the Bay Area and are parents of two thriving adult children and one adored Goldendoodle.

Cancellation Policy

Life happens. We understand that there will be times when you cannot attend a workshop that you have registered and paid for. We strive to be as helpful and flexible as possible when things out of your control happen. Please visit our FAQ page for detailed information about our cancellation policy and answers to frequently asked questions about enrollment and membership.